WO2016039781A1 - Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine - Google Patents
Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine Download PDFInfo
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- WO2016039781A1 WO2016039781A1 PCT/US2014/061030 US2014061030W WO2016039781A1 WO 2016039781 A1 WO2016039781 A1 WO 2016039781A1 US 2014061030 W US2014061030 W US 2014061030W WO 2016039781 A1 WO2016039781 A1 WO 2016039781A1
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- Prior art keywords
- chloro
- pyrazol
- pyridine
- methyl
- pyridin
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- HGFVBJHWMMMCRU-UHFFFAOYSA-N Cc1c[n](-c2cccnc2)nc1Cl Chemical compound Cc1c[n](-c2cccnc2)nc1Cl HGFVBJHWMMMCRU-UHFFFAOYSA-N 0.000 description 2
- MAWGAAFDEZVGPE-UHFFFAOYSA-N CC(C1)C(Cl)=NN1c1cccnc1 Chemical compound CC(C1)C(Cl)=NN1c1cccnc1 MAWGAAFDEZVGPE-UHFFFAOYSA-N 0.000 description 1
- SXUMSCJUXIVSFX-UHFFFAOYSA-N CCNc1c[n](-c2cccnc2)nc1Cl Chemical compound CCNc1c[n](-c2cccnc2)nc1Cl SXUMSCJUXIVSFX-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
Definitions
- This disclosure relates to the field of preparation of 3-(3-chloro- lH-pyrazol-l- yl)pyridine and intermediates therefrom. These intermediates are useful in the preparation of certain pesticides.
- US 20130288893(A1) describes certain (3-halo- l-(pyridin-3-yl)- lH-pyrazol-4- yl)amides and carbamates and their use as pesticides.
- the processes therein to prepare these amides and carbamates result in low yields, rely on a starting material that is difficult to prepare (3-chloropyrazole), and provide a product that is difficult to isolate in a pure form. It would be desirable to have a process for preparing 3-(3-chloro-lH-pyrazol- l-yl)pyridine that avoids these problems.
- alkyl denotes branched or unbranched hydrocarbon chains.
- alkoxide means an alkyl further consisting of a carbon- oxygen single bond, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, and iert-butoxy.
- the present disclosure provides an alternative process for preparing 3-(3-chloro- lH- pyrazol-l-yl)pyridine (5b) by cyclizing 3-hydrazinopyridine-dihydrochloride with an alkyl methacrylate to provide 4-methyl- l-(pyridin-3-yl)pyrazolidin-3-one (1), by chlorinating (1) to provide 3-(3-chloro-4-methyl-4,5-dihydro-lH-pyrazol-l-yl)pyridine (2), by oxidizing (2) to provide 3-(3-chloro-4-methyl- lH-pyrazol-l-yl)pyridine (3), by further oxidizing (3) to provide 3-chloro-l-(pyridin-3-yl)- lH-pyrazole-4-carboxylic acid (4), and by decarboxylating (4) to provide 3-(3-chloro- lH-pyrazol- l-yl)pyridine (5b).
- the present disclosure concerns
- R represents (Q-C. alkyl
- Scheme 1 outlines this process for preparing 3-(3-chloro- lH-pyrazol-l-yl)pyridine (5b).
- step la 3-hydrazinopyridine- dihydrochloride is cyclized with a (Q-C. alkyl methacrylate, in a solution further comprising a (CrC 4 ) alkyl alcohol and an alkali metal (Cr C 4 ) alkoxide, to provide 4-methyl-l-(pyridin-3-yl)pyrazolidin-3-one (1).
- Step a is conducted at a temperature from about 25 °C to about 80 °C. While stoichiometric amounts of 3- hydrazinopyridine-dihydrochloride and (Q-C.
- alkyl methacrylate may be used, it is often convenient to use about a 1.5 fold to about a 2 fold excess of (CrC 4 ) alkyl methacrylate compared to 3-hydrazinopyridine-dihydrochloride.
- the (CrC 4 ) alkyl alcohol is preferably selected from methanol, ethanol, propanol, butanol, and mixtures thereof.
- the alkali metal (C - C 4 ) alkoxide is preferably selected from sodium methoxide, sodium ethoxide, and mixtures thereof.
- 3-hydrazinopyridine- dihydrochloride is cyclized with methyl methacrylate in the presence of sodium ethoxide and ethanol and this mixture is heated at about 50 °C.
- the crude 4-methyl-l-(pyridin-3-yl)pyrazolidin-3-one (1) is used as is without further purification or isolation.
- step lb 4-methyl-l-(pyridin-3-yl)pyrazolidin-3-one (1) is chlorinated with a chlorinating reagent in an organic solvent at a temperature from about 25 °C to about 100 °C to provide 3-(3-chloro-4-methyl-4,5-dihydro-lH-pyrazol-l-yl)pyridine (2).
- Suitable chlorinating reagents include phosphoryl chloride (phosphorous oxychloride), phosphorus pentachloride, and mixtures thereof. Phosphoryl chloride is currently preferred.
- the chlorination is performed in an organic solvent that does not substantially react with the chlorinating reagent.
- Suitable solvents include nitriles such as acetonitrile. It is currently preferred to use phosphoryl chloride as the chlorinating reagent and acetonitrile as the solvent.
- 4-methyl-l-(pyridin-3-yl)pyrazolidin-3-one (1) in acetonitrile is chlorinated with phosphoryl chloride and the mixture is heated to about 75 °C.
- the 3-(3-chloro- 4-methyl-4,5-dihydro-lH-pyrazol-l-yl)pyridine (2) can be isolated and purified by standard techniques.
- step lc 3-(3-chloro-4-methyl-4,5-dihydro-lH-pyrazol-l-yl)pyridine (2) is oxidized with an oxidant in an organic solvent at a temperature of about 25 °C to about 100 °C to provide 3-(3-chloro-4-methyl-lH-pyrazol-l-yl)pyridine (3).
- Suitable oxidants include copper(I) chloride in the presence of oxygen, potassium ferricyanide, and manganese(IV) oxide. It is often convenient to use about a 1.5 fold to about a 15 fold excess of oxidant compared to 3-(3- chloro-4-methyl-4,5-dihydro-lH-pyrazol-l-yl)pyridine (2).
- the oxidation is performed in a solvent that does not substantially react with the oxidant.
- suitable solvents include water, N,N- dimethylformamide, N-methylpyrrolidinone, dichloromethane, iert-butanol, nitriles such as acetonitrile, aromatic hydrocarbons such as toluene, and mixtures thereof.
- copper(I) chloride in the presence of oxygen as the oxidant, with N,N- dimethylformamide, N-methylpyrolidinone, and mixtures thereof as the solvent.
- potassium -ferricyanide as the oxidant, with water as the solvent.
- manganese(IV) oxide as the oxidant, with dichloromethane, tert-butanol, acetonitrile, toluene, and mixtures thereof as the solvent. It is also preferred to use
- 3-(3-chloro-4-methyl-4,5-dihydro-lH-pyrazol-l-yl)pyridine (2) in acetonitrile is oxidized with manganese(IV) oxide and the mixture is heated at about 40 °C.
- the 3-(3-chloro-4-methyl-lH-pyrazol-l-yl)pyridine (3) can be isolated and purified by standard techniques.
- step Id 3-(3-chloro-4-methyl-lH-pyrazol-l-yl)pyridine (3) is further oxidized with an oxidant in a protic solvent at a temperature of about 50 °C to about 100 °C to provide 3- chloro-l-(pyridin-3-yl)-lH-pyrazole-4-carboxylic acid (4).
- Suitable oxidants include potassium permanganate and sodium permanganate. It is often convenient to use about a 2.5 fold to about 5 a 4.5 fold, preferably about a 3.0 fold excess of oxidant compared to 3-(3-chloro-4-methyl-lH- pyrazol-l-yl)pyridine (3).
- the oxidation is performed in a protic solvent that does not substantially react with the oxidant.
- Suitable solvents include water, ie/t-butanol, tert-amy ⁇ alcohol, and mixtures thereof.
- 3-(3-chloro-4-methyl-lH-pyrazol-l-yl)pyridine (3) is further o oxidized by sodium permanganate in water and iert-butanol and heated at about 80 °C.
- the 3- chloro-l-(pyridin-3-yl)-lH-pyrazole-4-carboxylic acid (4) can be isolated and purified by standard techniques.
- step le 3-chloro-l-(pyridin-3-yl)-lH-pyrazole-4-carboxylic acid (4) is
- Suitable copper oxide sources include copper(I) oxide and copper(II) oxide as well as mixtures thereof. It is convenient to use about 5 wt to about 20 wt of copper oxide based on 3-chloro- l-(pyridin-3-yl)-lH-pyrazole-4-carboxylic acid (4).
- Suitable solvents include N,N- o dimethylformamide, N,N-dimethylacetamide, N-methylpyrrolidinone, and mixtures thereof.
- 3-chloro-l-(pyridin-3-yl)-lH-pyrazole-4-carboxylic acid (4) and copper(I) oxide are mixed with N,N-dimethylacetamide and heated to about 125 °C.
- the 3- (3-chloro-lH-pyrazol-l-yl)pyridine (5b) can be isolated and purified by standard techniques.
- step 2a 3-(3-chloro-lH-pyrazol- l-yl)pyridine (5b) is nitrated with nitric acid ( ⁇ 3 ), preferably in the presence of sulfuric acid (H 2 S0 4 ) to yield 3-(3-chloro-4-nitro-lH- pyrazol-l-yl)pyridine (2-6).
- the nitration may be conducted at temperatures from about -10 °C to about 30 °C.
- step 2b 3-(3-chloro-4-nitro- lH-pyrazol- l-yl)pyridine (2-6) is reduced to yield 3- chloro- l-(pyridin-3-yl)- lH-pyrazol-4-amine (2-7).
- 3-(3-chloro-4-nitro- lH- pyrazol-l-yl)pyridine (2-6) may be reduced with iron in acetic acid (AcOH).
- 3-(3-Chloro-4- nitro- lH-pyrazol- l-yl)pyridine (2-6) may also be reduced with iron and ammonium chloride (NH 4 C1).
- this reduction may be carried out using other techniques in the art, for example, 3-(3-chloro-4-nitro-lH-pyrazol-l-yl)pyridine (2-6) may be reduced using palladium on carbon in the presence of hydrogen (H 2 ). This reaction may be conducted at temperatures from about -10 °C to about 30 °C.
- step 2c 3-chloro- l-(pyridin-3-yl)-lH-pyrazol-4-amine (2-7) is acylated with acetylating agents such as acetyl chloride or acetic anhydride, preferably acetic anhydride (Ac 2 0) to yield N-(3-chloro- l-(pyridin-3-yl)- lH-pyrazol-4-yl)acetamide (2-8).
- the acylation is conducted in the presence of a base, preferably an inorganic base, such as, sodium bicarbonate (NaHC0 3 ), and preferably, a polar solvent, such as ethyl acetate and/or tetrahydrofuran. This reaction may be conducted at temperatures from about -10 °C to about 30 °C.
- N-(3-chloro-l-(pyridin-3-yl)- lH-pyrazol-4-yl)acetamide (2-8) is alkylated with ethyl bromide (EtBr) in the presence of a base, such as sodium hydride (NaH) or sodium ie/t-butoxide (NaOi-Bu), in a polar aprotic solvent, such as tetrahydrofuran, at temperatures from about 20 °C to about 40 °C, over a period of time of about 60 hours to about 168 hours, to yield N-(3-chloro-l-(pyridin-3-yl)- lH-pyrazol-4-yl)-N-ethylacetamide (2-9).
- a base such as sodium hydride (NaH) or sodium ie/t-butoxide (NaOi-Bu)
- a polar aprotic solvent such as tetrahydrofuran
- iodide additive such as potassium iodide (KI) or tetrabutylammonium iodide (TBAI) can decrease the time necessary for the reaction to occur to about 24 hours. It has also been discovered that heating the reaction at about 50 °C to about 70 °C in a sealed reactor (to prevent loss of ethyl bromide) also decreases the reaction time to about 24 hours.
- KI potassium iodide
- TBAI tetrabutylammonium iodide
- step 2e N-(3-chloro-l-(pyridin-3-yl)- lH-pyrazol-4-yl)-N-ethylacetamide (2-9) is treated with hydrochloric acid in water at temperatures from about 50 °C to about 90 °C, to yield 3-chloro-N-ethyl-l-(pyridin-3-yl)- lH-pyrazol-amine (2-10).
- Steps d and e of Scheme 2 may also be performed without the isolation of N-(3-chloro- l-(pyridin-3-yl)-lH-pyrazol-4-yl)- N-ethylacetamide (2-8).
- step 2f 3-chloro-N-ethyl- l-(pyridin-3-yl)-lH-pyrazol-amine (2-10) is acylated with 3-((3,3,3-trifluoropropyl)thio)propanoyl chloride in the presence of a base preferably, sodium bicarbonate to yield pesticidal (3-halo- l-(pyridin-3-yl)-lH-pyrazol-4-yl)amide (2- 11).
- the reaction may also be conducted in the absence of a base to yield pesticidal (3-halo- l-(pyridin-3- yl)-lH-pyrazol-4-yl)amide (2- 11).
- step 2g pesticidal (3-halo- l-(pyridin-3-yl)- lH-pyrazol-4-yl)amide (2- 11) is oxidized with hydrogen peroxide (H 2 0 2 ) in methanol to yield pesticidal (3-halo- l-(pyridin-3-yl)-lH- pyrazol-4-yl)amide (2-12).
- 3-hydrazinopyridine- dihydrochloride (15.0 g, 82.4 mmol).
- Sodium ethoxide (21 wt in ethanol, 92.3 mL, 247 mmol) was added over 5 minutes and the pot temperature increased from 23 °C to 38 °C.
- the resultant light brown-slurry was stirred for 10 minutes.
- Methyl methacrylate (17.7 mL, 165 mmol) was added slowly over 15 minutes and the pot temperature remained at 38 °C. The yellow mixture was stirred at 50 °C under nitrogen for 4 hours.
- reaction mixture was carefully diluted into water, basified with sodium hydroxide (50 wt in water) and extracted with ethyl acetate. Analysis of the organic layer indicated that the reaction was essentially complete.
- the reaction mixture was carefully added to ice cold water (100 mL) at ⁇ 20 °C. It was basified with sodium hydroxide (50 wt in water) at ⁇ 20 °C. The resulting light yellow suspension was stirred for 2 hours and filtered.
- N-(3-chloro-l-(pyridin-3-yl)-lH- pyrazol-4-yl)acetamide (2.57 g, 9.44 mmol)
- tetrahydrofuran 55 mL
- sodium ie/t-butoxide 1.81 g, 18.9 mmol
- the suspension was stirred for 5 minutes then ethyl bromide (1.41 mL, 18.9 mmol), and tetrabutylammonium iodide (67 mg, 0.2 mmol) were added.
- the resulting gray colored suspension was then heated to 38 °C.
- the reaction was analyzed after 3 hours and found to have gone to 81% completion, after 24 hours the reaction was found to have gone to completion.
- the reaction mixture was allowed to cool to ambient temperature and quenched with ammonium hydroxide/formic acid (HC0 2 H) buffer (10 mL).
- the mixture was then diluted with tetrahydrofuran (40 mL), ethyl acetate (120 mL), and saturated sodium bicarbonate solution in water (30 mL).
- the layers were separated and the aqueous layer was extracted with ethyl acetate (2 x 30 mL).
- the organic layers were combined and silica gel (37 g) was added.
- N-(3-chloro-l-(pyridin-3-yl)- lH- pyrazol-4-yl)acetamide 5 g, 21.13 mmol
- tetrahydrofuran 50 mL
- Sodium iert-butoxide (4.06 g, 42.3 mmol) was added (causing a temperature rise from 22 °C to 27.6 °C), followed by ethyl bromide (6.26 mL, 85 mmol).
- the reaction was stirred at 35 °C for 144 h at which point only 3.2% (AUC) starting material remained.
- the reaction mixture was concentrated to give a brown residue, which was dissolved in 1 N hydrochloric acid (106 mL, 106 mmol) and heated at 80 °C for 24 hours, at which point HPLC analysis indicated that the starting material had been consumed.
- the reaction was cooled to 20 °C and basified with sodium hydroxide (50 wt% in water) to pH>9.
- the resulting suspension was stirred at 20 °C for 1 hour and filtered.
- the filter cake was rinsed with water (25 mL) to afford a brown solid (5.18 g).
- the resulting crude product was dissolved in ethyl acetate and passed through a silica gel plug (50 g) using ethyl acetate (500 mL) as eluent.
- N-(3-Chloro-l-(pyridin-3-yl)- lH-pyrazol-4-yl)-N-ethyl-3-((3,3,3-trifluoropropyl)thio) propanamide (57.4 g, 141 mmol) was stirred in methanol (180 mL). To the resulting solution was added hydrogen peroxide (43.2 mL, 423 mmol) dropwise using a syringe. The solution was stirred at room temperature for 6 hours, at which point LCMS analysis indicated that the starting material was consumed. The mixture was poured into dichloromethane (360 mL) and washed with aqueous sodium carbonate (Na 2 C0 3 ).
- GPA is the most significant aphid pest of peach trees, causing decreased growth, shriveling of leaves, and the death of various tissues. It is also hazardous because it acts as a vector for the transport of plant viruses, such as potato virus Y and potato leafroll virus to members of the nightshade /potato family Solanaceae, and various mosaic viruses to many other food crops. GPA attacks such plants as broccoli, burdock, cabbage, carrot, cauliflower, daikon, eggplant, green beans, lettuce, macadamia, papaya, peppers, sweet potatoes, tomatoes, watercress and zucchini among other plants. GPA also attacks many ornamental crops such as carnations, chrysanthemum, flowering white cabbage, poinsettia and roses. GPA has developed resistance to many pesticides.
- the seedlings were infested with 20-5- GPA (wingless adult and nymph stages) one day prior to chemical application.
- Test compounds (2 mg) were dissolved in 2 mL of acetone/methanol (1: 1) solvent, forming stock solutions of 1000 ppm test compound.
- the stock solutions were diluted 5X with 0.025% Tween 20 in water to obtain the solution at 200 ppm test compound.
- a hand-held aspirator-type sprayer was used for spraying a solution to both sides of the cabbage leaves until runoff.
- Reference plants (solvent check) were sprayed with the diluent only containing 20% by volume acetone/methanol (1: 1) solvent. Treated plants were held in a holding room for three days at approximately 25 °C and ambient relative humidity (RH) prior to grading. Evaluation was conducted by counting the number of live aphids per plant under a microscope. Percent Control was measured by using Abbott's correction formula (W.S. Abbott, "A Method of Computing the Effectiveness of an Insecticide" J. Econ. Entomol 18 (1925), pp.265-267) as follows.
- Table 1 GPA (MYZUPE) and sweetpotato whitefly-crawler (BEMITA) Rating Table.
- Bemisia tabaci The sweetpotato whitefly, Bemisia tabaci (Gennadius), has been recorded in the United States since the late 1800s. In 1986 in Florida, Bemisia tabaci became an extreme economic pest. Whiteflies usually feed on the lower surface of their host plant leaves. From the egg hatches a minute crawler stage that moves about the leaf until it inserts its microscopic, threadlike mouthparts to feed by sucking sap from the phloem.
- Adults and nymphs excrete honeydew (largely plant sugars from feeding on phloem), a sticky, viscous liquid in which dark sooty molds grow.
- honeydew can stick cotton lint together, making it more difficult to gin and therefore reducing its value.
- Sooty mold grows on honeydew-covered substrates, obscuring the leaf and reducing photosynthesis, and reducing fruit quality grade. It transmitted plant-pathogenic viruses that had never affected cultivated crops and induced plant physiological disorders, such as tomato irregular ripening and squash silverleaf disorder. Whiteflies are resistant to many formerly effective pesticides.
- the stock solutions were diluted 10X with 0.025% Tween 20 in water to obtain a test solution at 200 ppm.
- a hand-held Devilbliss sprayer was used for spraying a solution to both sides of cotton leaf until runoff.
- Reference plants (solvent check) were sprayed with the diluent only.
- Treated plants were held in a holding room for 8-9 days at approximately 82 °F and 50% RH prior to grading. Evaluation was conducted by counting the number of live nymphs per plant under a microscope. Pesticidal activity was measured by using Abbott's correction formula (see above) and presented in Table 1.
- GPA MYZUPE
- sweetpotato whitefly-crawler BEMITA Rating Table
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- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
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- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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EP14901610.7A EP3191455A4 (en) | 2014-09-12 | 2014-10-17 | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
JP2017513512A JP2017528469A (ja) | 2014-09-12 | 2014-10-17 | 3−(3−クロロ−1h−ピラゾール−1−イル)ピリジンの調製方法 |
KR1020177009470A KR20170058388A (ko) | 2014-09-12 | 2014-10-17 | 3-(3-클로로-1h-피라졸-1-일)피리딘의 제조 방법 |
BR112017004613A BR112017004613A2 (pt) | 2014-09-12 | 2014-10-17 | processo para a preparação de 3-(3-cloro-1h-pirazol-1-il)piridina |
CA2960985A CA2960985A1 (en) | 2014-09-12 | 2014-10-17 | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
CN201480083285.8A CN107074775A (zh) | 2014-09-12 | 2014-10-17 | 3‑(3‑氯‑1h‑吡唑‑1‑基)吡啶的制备方法 |
IL250984A IL250984A0 (en) | 2014-09-12 | 2017-03-07 | Process for preparing 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
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JP2016536295A (ja) | 2013-10-17 | 2016-11-24 | ダウ アグロサイエンシィズ エルエルシー | 有害生物防除性化合物の製造方法 |
CN105636441B (zh) | 2013-10-17 | 2018-06-15 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
KR20160072155A (ko) | 2013-10-17 | 2016-06-22 | 다우 아그로사이언시즈 엘엘씨 | 살충성 화합물의 제조 방법 |
MX2016004948A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de un compuesto pesticida. |
MX2016004946A (es) | 2013-10-17 | 2016-06-28 | Dow Agrosciences Llc | Procesos para la preparacion de compuestos plaguicidas. |
CA2925914A1 (en) | 2013-10-17 | 2015-04-23 | Dow Agrosciences Llc | Processes for the preparation of pesticidal compounds |
CN105636445B (zh) | 2013-10-17 | 2018-12-07 | 美国陶氏益农公司 | 制备杀虫化合物的方法 |
US9249122B1 (en) | 2014-07-31 | 2016-02-02 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1H-pyrazol-1-yl)pyridine |
CA2954345A1 (en) | 2014-07-31 | 2016-02-04 | Dow Agrosciences Llc | Process for the preparation of 3-(3-chloro-1h-pyrazol-1-yl)pyridine |
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- 2014-10-17 JP JP2017513512A patent/JP2017528469A/ja active Pending
- 2014-10-17 CN CN201480083285.8A patent/CN107074775A/zh active Pending
- 2014-10-17 KR KR1020177009470A patent/KR20170058388A/ko not_active Application Discontinuation
- 2014-10-17 WO PCT/US2014/061030 patent/WO2016039781A1/en active Application Filing
- 2014-10-17 US US14/517,361 patent/US9085552B1/en not_active Expired - Fee Related
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US9663489B2 (en) | 2017-05-30 |
US9422265B2 (en) | 2016-08-23 |
US9156813B1 (en) | 2015-10-13 |
BR112017004613A2 (pt) | 2017-12-05 |
US20180141929A1 (en) | 2018-05-24 |
US20160075681A1 (en) | 2016-03-17 |
US9085552B1 (en) | 2015-07-21 |
EP3191455A4 (en) | 2018-01-24 |
CN107074775A (zh) | 2017-08-18 |
EP3191455A1 (en) | 2017-07-19 |
US9896430B2 (en) | 2018-02-20 |
IL250984A0 (en) | 2017-04-30 |
CA2960985A1 (en) | 2016-03-17 |
TW201613893A (en) | 2016-04-16 |
US20170217924A1 (en) | 2017-08-03 |
KR20170058388A (ko) | 2017-05-26 |
US20160332986A1 (en) | 2016-11-17 |
AR098113A1 (es) | 2016-05-04 |
JP2017528469A (ja) | 2017-09-28 |
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